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About Skypoint

Skypoint is a HITRUST r2–certified Agentic AI platform for healthcare operations, designed to accelerate productivity and operational efficiency across healthcare organizations. Our platform enables healthcare providers, payers, and senior care organizations to unify fragmented data, model industry-specific ontologies, and deploy AI agents that automate workflows and support better, faster decision-making.

Founded in 2020 in Portland, Oregon, Skypoint has grown to a team of over 75 employees and now serves more than 100 customers. We are proud to be recognized on Deloitte’s 2024 and 2025 Technology Fast 500™, celebrating the fastest-growing technology companies in North America, and to be featured on the INC. 5000 list in 2025, reflecting our strong and sustained revenue growth over the past three years. 

Location: Remote
Shift: PST/PDT Hours
Experience: 5+ Years
Certification: PMP - Mandatory

About the Role

We are looking for an experienced Senior Technical Project Manager to lead the end-to-end planning, execution, and delivery of complex customer implementations and strategic technology initiatives across Skypoint’s AI-powered healthcare platform.

This is a highly customer-facing role with frequent interaction with U.S.-based customers, senior stakeholders, and cross-functional internal teams. Excellent verbal and written communication skills, proven customer-facing experience, PMP certification, strong AI-tool proficiency, and availability to work PST/PDT hours are mandatory.

You will serve as a key bridge between customers and our Product, Engineering, Data, AI, and Customer Success teams—understanding customer requirements, managing expectations, driving execution, and ensuring successful delivery.

Key Responsibilities

• Own and drive end-to-end delivery of customer implementations, platform deployments, integrations, and strategic technical initiatives.

• Develop and manage detailed project plans, timelines, milestones, dependencies, resource requirements, and delivery schedules.

• Serve as a primary point of contact for customers throughout implementation and project delivery.

• Lead customer onboarding, implementation planning, status reviews, technical coordination, governance meetings, UAT, go-live, and post-launch activities.

• Partner closely with Product, Engineering, Data, AI, Customer Success, and Operations teams to align priorities and execution.

• Manage multiple concurrent projects while balancing scope, resources, risks, dependencies, and deadlines.

• Identify blockers and risks early and proactively drive them to resolution.

• Translate customer and business requirements into structured technical workstreams, milestones, and actionable deliverables.

• Facilitate Agile ceremonies including sprint planning, stand-ups, reviews, retrospectives, and release planning.

• Work closely with technical teams to understand APIs, integrations, cloud platforms, data pipelines, software architecture, and AI-powered solutions.

• Communicate project progress, timelines, risks, dependencies, and outcomes clearly to customers, executives, and technical teams.

• Manage customer expectations and maintain alignment between business goals, technical feasibility, and project scope.

• Establish project governance, documentation, status reporting, dashboards, and project health metrics.

• Drive continuous improvement in project management processes, tools, templates, and delivery practices.

Required Qualifications

• 5+ years of experience managing technical projects, SaaS implementations, enterprise software deployments, or technology programs.

• PMP certification is mandatory.

• Excellent verbal and written communication skills are mandatory.

• Proven customer-facing experience is mandatory, including managing customer meetings, expectations, escalations, implementation discussions, and project updates.

• Demonstrated ability to communicate confidently with senior customer stakeholders and executives.

• Strong experience managing cross-functional projects involving Engineering, Product, Data, AI, and customer-facing teams.

• Strong understanding of Agile, Scrum, and modern software development lifecycle practices.

• Technical understanding of APIs, integrations, cloud platforms, data pipelines, databases, SaaS applications, and software architecture.

• Strong project planning, stakeholder management, risk management, problem-solving, and decision-making skills.

• Experience using tools such as Jira, Azure DevOps, Asana or equivalent.

• Must be comfortable working remotely during PST/PDT hours.

Preferred Qualifications

• Prior experience working directly with U.S.-based customers and stakeholders - Valid U.S. B1/B2 visa is preferred, as the role may require occasional business travel to the United States.

• Experience in healthcare technology, healthcare operations, payer, provider, or senior care environments.

• Experience managing projects involving AI, Generative AI, data engineering, analytics, or cloud technologies.

• Experience with Microsoft Azure or other major cloud platforms.

• Additional certifications such as PMI-ACP, CSM, or SAFe are a plus.

• Familiarity with regulated environments and frameworks such as HIPAA, HITRUST, or SOC 2.

• Experience working in a high-growth startup or scale-up environment.

   

Life at Skypoint

Life at Skypoint is fast-paced, collaborative, and focused on using AI and modern technology to solve real-world healthcare challenges. Our teams work closely across Product, Engineering, Data, and Customer Success, giving you the opportunity to see the direct impact of what you build.

We support continuous learning, mentorship, ownership, and career growth while giving team members opportunities to work on emerging AI and healthcare technologies.

Why Join Skypoint

• Lead high-impact initiatives across AI, data, cloud, and healthcare technology.

• Work directly with U.S.-based healthcare customers and senior stakeholders.

• Collaborate with experienced Product, Engineering, Data, AI, and Customer Success teams.

• Gain exposure to cutting-edge Agentic AI technologies.

• Competitive compensation and comprehensive benefits.

• Remote work flexibility.

• Continuous learning and career growth opportunities.

• Join a fast-growing company recognized on Deloitte’s Technology Fast 500™.

   

Skypoint is an Equal Opportunity Employer. We do not discriminate based on race, color, religion, sex, national origin, age, disability, veteran status, or any other protected characteristic.